1. Field of the Invention
This invention relates to a novel class of esters of 2-phenylalkanenitriles and to antifungal compositions containing such esters.
2. Description of the Related Art
There are a number of chemical compounds disclosed in the art which are said to have antifungal and/or antibacterial activity. For example, U.S. Pat. No. 4,267,179 describes certain heterocyclic derivatives of (4-phenylpiperazine-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)-1H-imidazoles and 1H-1,2,4-triazoles which are taught to be useful as antifungal and antibacterial agents. U.S. Pat. No. 4,709,078 discloses certain acrylates, such as methyl α-(2-benzyloxy phenyl)-β-methoxyacrylate, and certain fungicidal compositions containing such acrylate compounds. U.S. Pat. No. 3,485,925 describes certain ortho-haloatroponitriles which are said to be useful in inhibiting the growth of microorganisms. The novel compounds of the present invention differ from the prior art compounds in that they are not imidazoles, triazoles, acrylates or atroponitriles, but instead are esters of substituted phenylalkanenitriles, which have been found to be highly effective antifungal agents even at relatively low concentrations.
The syntheses of various synthetic intermediates, including certain esters of substituted phenylalkanenitriles, derived from tertiary arylic alcohols are disclosed in the article: “Lipase-catalyzed remote kinetic resolution of arylic nitrites with adjacent quaternary chiral center and the determination of their absolute configuration”, Dai Sig Im, Chan Seong Cheong, So Ha Lee, Journal of Molecular Catalysis B: Enzymatic 26 (2003) 131-143. The ester compounds disclosed in this article are not disclosed to have antifungal or antibacterial activity, and differ structurally from the esters of the present invention in that they are substituted in the alpha position to the nitrile group. It is an important feature of the esters of the present invention that the alpha position to the nitrile group not be substituted.